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Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides

Mathias Pichler1, Johanna Novacek, Raphaël Robiette

  • 1Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, Austria. Mario.waser@jku.at.

Organic & Biomolecular Chemistry
|December 19, 2014
PubMed

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
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